The reaction of fumonisin B1 with the reducing sugar D-glucose can block the primary amine group of fumonisin B1 and may detoxify this mycotoxin. A method to separate hundred milligram quantities of fumonisin B1-glucose reaction products from the excess D-glucose with a reversed-phase C18 cartridge was developed. Mass spectrometry revealed that there were four primary products in this chain reaction when fumonisin B1 was heated with D-glucose at 65 C for 48 h: N-methyl-fumonisin B1, N-carboxymethylfumonisin B1, N-(3-hydroxyacetonyl)-fumonisin B1, and N-(2-hydroxy, 2-car-boxyethyl)-fumonisin B1. The N-(1-deoxy-D-fructos-1-yl) fumonisin B1 (fumonisin B1-glucose Schiff 's base) was detected by mass spectrometry when fumonisin B1 was heated with D-glucose at 60 C. The nonenzymatic browning reaction of fumonisin B1 with excess D-glucose followed apparent first-order kinetics. The activation energy, Ea, was 105.7 kJ/mol.
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AuthorsYun Lu, Laura Clifford, Catherine C.
It was hypothesized that a simplified and efficient strategy could be developed for large-scale production and purification of the mycotoxin deoxynivalenol from Fusarium graminearum rice cultures for toxicological studies. F. graminearum R6576 was cultured on rice and extracted with methanol, and the extract was concentrated and subjected to silica gel low-pressure liquid chromatography (LPLC) under a hexane-acetone gradient system. Deoxynivalenol isolation was monitored by thin-layer chromatography, and fractions containing deoxynivalenol were pooled, concentrated, and applied to a second LPLC column under the same conditions. An enriched deoxynivalenol fraction was obtained, which yielded a crystalline material. Repeated crystallization yielded spectroscopically pure deoxynivalenol. The identity of this compound was confirmed by HPLC comparison to an authentic deoxynivalenol standard, FABMS analysis, and comparison of the (1)H and (13)C NMR spectra with published data. This simplified purification scheme eliminated many laborious steps and equipment previously required to obtain gram quantities of crystalline deoxynivalenol for biological testing in animal models.
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